1-Pyrenebutanol → HCID 54018264, compound

HRID 1751896Notes

Reaction equation

HRID 1751896 reaction equation
[C:1]1([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:1]1([CH2:17][CH2:18][CH2:19][CH:20]=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 27626721-PyrenebutanolHCID 178418287HCID 178418287, compound

Product 1

HCID 54018264HCID 54018264, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

10 mL of methylene chloride was added to 1.097 g (4 mmol) of 4-(pyren-1-yl) butyl alcohol and stirred vigorously at room temperature for 10 min hour. The reaction was followed by addition of 1.292 g (1.5 Eq.) of PCC (Pyridinium chlorochromate) in 10 mL methylene chloride and the reaction mixture was stirred for 2 h. The reaction mixture was then diluted with 5 volumes of anhydrous ether (100 mL) and washed with 1:1 brine:water, saturated aq. Na2SO3 solution, and brine, respectively, dried over anhydrous Na2SO4 and concentrated to give the aldehyde. The crude product was purified by silica gel flash chromatography (hexanes: ethyl acetate, 9:1, rf: 0.4) to yield 1.06 g (97%). Most of the crude products were very clean and could be used directly for further applications.

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. washwashed with 1:1 brine
  3. dry with materialwater, saturated aq. Na2SO3 solution, and brine, respectively, dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f976b8f5bf0741e0a5360b2d491ec1fd
Source dataset
uspto-grants-2015_10
Patent number
US09162885B2

Reaction notes

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